EP1414385B1 - Adhesif dentaire simple a auto-amorcage - Google Patents

Adhesif dentaire simple a auto-amorcage Download PDF

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Publication number
EP1414385B1
EP1414385B1 EP02750441A EP02750441A EP1414385B1 EP 1414385 B1 EP1414385 B1 EP 1414385B1 EP 02750441 A EP02750441 A EP 02750441A EP 02750441 A EP02750441 A EP 02750441A EP 1414385 B1 EP1414385 B1 EP 1414385B1
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EP
European Patent Office
Prior art keywords
unsubstituted
substituted
self
etching
dental adhesive
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP02750441A
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German (de)
English (en)
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EP1414385A1 (fr
Inventor
Joachim E. Klee
Uwe Walz
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Dentsply Sirona Inc
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Dentsply International Inc
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S522/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S522/908—Dental utility

Definitions

  • the invention relates to dental adhesive compositions for bonding dental restoratives to dentin and enamel. More specifically the invention provides a one-part self-etching, self-priming dental adhesive composition comprising hydrolysis stable polymerizable acidic adhesive monomers.
  • self-etching, self-priming dental adhesives are composed of two-part systems due to stability issues of the polymerizable acidic monomers.
  • Typical compositions are known from US 6,174,935.
  • the stability issues are due to the hydrolysis of acidic and adhesive monomers in water or water/solvent mixtures. Therefore the acidic and adhesive monomers are stored water-free and mixed with the aqueous part just before application
  • Two-part self-etching, self-priming dental adhesive systems are either applied sequentially or in one step after mixing the two parts, Both procedures have inherent disadvantages due to clinical complications which might occur inbetween sequential steps (saliva or blood contamination) or due to dosing problems when mixing is required prior to the application of the self-etching adhesive.
  • the present invention provides a hydrolysis stable one-part self-etching, self-priming dental adhesive based on (meth)acrylamides and use thereof in polymerizable dental adhesive compositions containing
  • the hydrolysis stable one-part self-etching, self-priming dental adhesive comprises at least a carboxylic acid, a phosphoric acid or a sulfuric acid group or most preferably at least a phosphonic or a sulfonic acid moiety.
  • the polymerizable (meth) acrylamide that comprises at least a phosphonic or sulfonic acid moiety is characterized by the following formulas: wherein
  • polymerizable (meth) acrylamide that comprises at least a phosphonic or sulfonic acid moiety polymerizable monomers are applied that also have an improved hydrolysis stability, that are characterized by the following formulas: wherein
  • the preferably used bis- and mono (meth) acrylamides are characterized by the following formulas:
  • compositions comprise at least a bis- or poly (meth) acrylamide, a polymerizable mono acrylamide, an initiator an inhibitor a stabilizer, water and/or an organic solvent.
  • the polymerization initiator is a thermal initiator, a redox-initiator or a photo initiator preferably used is champhor quinone.
  • radical absorbing monomers such as hydroquinone monomethylether, 2,6-di-tert.-butyl-p-cresol, tetramethyl piperidine N-oxyl radical, galvanoxyl radical.
  • the viscose residue was dissolved in 300 ml CH 2 Cl 2 and cooled to 0 °C.
  • the precipitating solid was removed and the filtrate was washed twice with 150 ml 1 n HCl, 150 ml 1n NaHCO 3 solution and with 150 ml water. Furthermore, the solution was dried over NaSO 4 and the solvent was removed. Than the solid was dissolved in Acetone again and dicyclohexyl urea was filtered of. Prior to remove the solvent, 0.197 g BHT was added, the product was dried in vacuum.

Claims (12)

  1. Adhésif dentaire en une partie, stable à l'hydrolyse, à auto-amorçage et auto-attaque chimique, comprenant
    (i) un (méth)acrylamide polymérisable acide qui comprend au moins un groupement acide organique ou inorganique, ledit (méth)acrylamide polymérisable acide étant choisi dans le groupe consistant en :
    Figure imgb0033
    Figure imgb0034
     dans lesquels
    R1 et R2 représentent indépendamment
    un atome d'hydrogène, ou
    un groupe alkyle en C1 à C18 substitué ou non substitué,
    un groupe cycloalkyle substitué ou non substitué,
    un groupe aryle ou hétéroaryle en C5 à C18 substitué ou non substitué, alkylaryle ou alkylhétéroaryle en C5 à C18 substitué ou non substitué,
    un groupe alkylaryle en C7 à C30 substitué ou non substitué,
    R3 et R4 représentent indépendamment
    un groupe alkylène en C1 à C18 difonctionnel substitué ou non substitué,
    un groupe cycloalkylène difonctionnel substitué ou non substitué,
    un groupe arylène ou hétéroarylène en C5 à C18 difonctionnel substitué ou non substitué,
    un groupe alkylarylène ou alkylhétéroarylène en C5 à C18 difonctionnel substitué ou non substitué,
    un groupe alkylène-arylène en C7 à C30 difonctionnel substitué ou non substitué ;
    n représente un nombre entier ;
    (ii) un monomère polymérisable choisi dans le groupe consistant en :
    Figure imgb0035
     dans lesquels
    R1 et R3 représentent indépendamment
    H, ou
    un groupe alkyle en C1 à C18 substitué ou non substitué,
    un groupe cycloalkyle substitué ou non substitué,
    un groupe aryle ou hétéroaryle en C5 à C18 substitué ou non substitué,
    un groupe alkylaryle ou alkylhétéroaryle en C5 à C18 substitué ou non substitué,
    un groupe alkylène-aryle en C7 à C30 substitué ou non substitué,
    R2 représente un groupe alkylène en C1 à C18 difonctionnel substitué ou non substitué,
    un groupe cycloalkylène difonctionnel substitué ou non substitué,
    un groupe arylène ou hétéroarylène en C5 à C18 difonctionnel substitué ou non substitué,
    un groupe alkylarylène ou alkylhétéroarylène en C5 à C18 difonctionnel substitué ou non substitué,
    un groupe alkylène-arylène en C7 à C30 difonctionnel substitué ou non substitué,
    R4 représente un groupe alkylène en C1 à C18 mono- ou polyfonctionnel substitué ou non substitué,
    un groupe cycloalkylène mono- ou polyfonctionnel substitué ou non substitué,
    un groupe arylène ou hétéroarylène en C5 à C18 mono- ou polyfonctionnel substitué ou non substitué,
    un groupe alkylarylène ou alkylhétéroarylène en C5 à C18 mono- ou polyfonctionnel substitué ou non substitué,
    un groupe alkylène-arylène en C7 à C30 mono- ou polyfonctionnel substitué ou non substitué n représente un nombre entier ; et
    (iii) un initiateur de polymérisation, un inhibiteur et un stabilisant.
  2. Adhésif dentaire en une partie, stable à l'hydrolyse, à auto-amorçage et auto-attaque chimique, suivant la revendication 1, dans lequel ledit monomère polymérisable est un mono- bis- ou poly(méth)acrylamide qui est choisi dans le groupe consistant en :
    Figure imgb0036
    Figure imgb0037
    Figure imgb0038
    Figure imgb0039
  3. Adhésif dentaire en une partie, stable à l'hydrolyse, à auto-amorçage et auto-attaque chimique, suivant la revendication 1 ou 2, dans lequel le (méth)acrylamide polymérisable acide est choisi dans le groupe consistant en :
    Figure imgb0040
    Figure imgb0041
    Figure imgb0042
    Figure imgb0043
  4. Adhésif dentaire en une partie, stable à l'hydrolyse, à auto-amorçage et auto-attaque chimique, suivant la revendication 1, constitué d'au moins un (méth)acrylamide polymérisable acide, de monomère polymérisable, d'un initiateur, d'un stabilisant, de pigments et d'une charge organique et/ou inorganique.
  5. Adhésif dentaire en une partie, stable à l'hydrolyse, à auto-amorçage et auto-attaque chimique, suivant la revendication 1, comprenant au moins un (méth)acrylamide polymérisable acide, un monomère polymérisable, un initiateur, un stabilisant, de l'eau ou un solvant organique.
  6. Adhésif dentaire en une partie, stable à l'hydrolyse, à auto-amorçage et auto-attaque chimique, suivant la revendication 1, comprenant au moins un (méth)acrylamide polymérisable acide, un monomère polymérisable, un initiateur, un stabilisant, des pigments, une charge organique et/ou inorganique, de l'eau et/ou un solvant organique.
  7. Adhésif dentaire en une partie, stable à l'hydrolyse, à auto-amorçage et auto-attaque chimique, suivant la revendication 1, dans lequel lesdits monomères polymérisables sont appliqués en une teneur de 0 à 90 % en poids.
  8. Adhésif dentaire en une partie, stable à l'hydrolyse, à auto-amorçage et auto-attaque chimique, suivant la revendication 1, dans lequel ledit initiateur de polymérisation est un initiateur thermique, un initiateur redox ou un photo-initiateur.
  9. Adhésif dentaire en une partie, stable à l'hydrolyse, à auto-amorçage et auto-attaque chimique, suivant la revendication 1, dans lequel ledit photo-initiateur est de préférence la camphoquinone.
  10. Adhésif dentaire en une partie, stable à l'hydrolyse, à auto-amorçage et auto-attaque chimique, suivant la revendication 1, dans lequel ladite charge est une charge inorganique et/ou une charge organique, la charge étant de préférence une nanocharge.
  11. Adhésif dentaire en une partie, stable à l'hydrolyse, à auto-amorçage et auto-attaque chimique, suivant la revendication 1, dans lequel ledit stabilisant est un monomère absorbant des radicaux, tel que l'éther monométhylique d'hydroquinone ou le 2,6-di-tertiobutyl-p-crésol.
  12. Adhésif dentaire en une partie, stable à l'hydrolyse, à auto-amorçage et auto-attaque chimique, suivant la revendication 1, dans lequel ledit solvant organique est de préférence l'acétone, l'éthanol ou.le tertiobutanol.
EP02750441A 2001-08-10 2002-08-06 Adhesif dentaire simple a auto-amorcage Expired - Lifetime EP1414385B1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US213303 1988-06-29
US31143301P 2001-08-10 2001-08-10
US311433P 2001-08-10
US10/213,303 US6812266B2 (en) 2001-08-10 2002-08-06 Hydrolysis stable one-part self-etching, self-priming dental adhesive
PCT/US2002/025005 WO2003013444A1 (fr) 2001-08-10 2002-08-06 Adhesif dentaire simple a auto-amorçage

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EP1414385A1 EP1414385A1 (fr) 2004-05-06
EP1414385B1 true EP1414385B1 (fr) 2006-12-20

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US (1) US6812266B2 (fr)
EP (1) EP1414385B1 (fr)
AT (1) ATE348590T1 (fr)
CA (1) CA2457347A1 (fr)
DE (1) DE60216930T2 (fr)
WO (1) WO2003013444A1 (fr)

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EP1414385A1 (fr) 2004-05-06
DE60216930D1 (de) 2007-02-01
ATE348590T1 (de) 2007-01-15
DE60216930T2 (de) 2007-04-05
US6812266B2 (en) 2004-11-02
WO2003013444A1 (fr) 2003-02-20
US20030055124A1 (en) 2003-03-20
CA2457347A1 (fr) 2003-02-20

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